CA2449994C - Method for telomerizing non-cyclic olefins - Google Patents

Method for telomerizing non-cyclic olefins Download PDF

Info

Publication number: CA2449994C
Authority: CA; Canada
Prior art keywords: alkyl; aryl; palladium; coo; branched
Prior art date: 2001-06-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA2449994A

Other languages

English (en)

French (fr)

Other versions

CA2449994A1 (en

Inventor

Dirk Rottger

Matthias Beller

Ralf Jackstell

Holger Klein

Klaus-Diether Wiese

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Evonik Operations GmbH

Original Assignee

Evonik Oxeno GmbH and Co KG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-06-09

Filing date

2002-05-04

Publication date

2010-10-19

2002-05-04 Application filed by Evonik Oxeno GmbH and Co KG filed Critical Evonik Oxeno GmbH and Co KG

2002-12-19 Publication of CA2449994A1 publication Critical patent/CA2449994A1/en

2010-10-19 Application granted granted Critical

2010-10-19 Publication of CA2449994C publication Critical patent/CA2449994C/en

2022-05-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 58
-1 cyclic olefins Chemical class 0.000 title claims abstract description 29
239000003054 catalyst Substances 0.000 claims abstract description 42
239000012038 nucleophile Substances 0.000 claims abstract description 30
239000000203 mixture Substances 0.000 claims abstract description 16
150000001336 alkenes Chemical class 0.000 claims abstract description 8
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 83
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 61
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
238000006243 chemical reaction Methods 0.000 claims description 40
239000003446 ligand Substances 0.000 claims description 26
229910052763 palladium Inorganic materials 0.000 claims description 19
239000000047 product Substances 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 16
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
229910006069 SO3H Inorganic materials 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
238000011065 in-situ storage Methods 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
150000001735 carboxylic acids Chemical class 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
229920005862 polyol Polymers 0.000 claims description 2
125000005270 trialkylamine group Chemical group 0.000 claims description 2
125000006686 (C1-C24) alkyl group Chemical group 0.000 claims 5
125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
239000007795 chemical reaction product Substances 0.000 claims 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
150000003077 polyols Chemical class 0.000 claims 1
150000003141 primary amines Chemical class 0.000 claims 1
150000003335 secondary amines Chemical class 0.000 claims 1
239000000243 solution Substances 0.000 description 14
150000001993 dienes Chemical class 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000002940 palladium Chemical class 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
239000002243 precursor Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
230000003797 telogen phase Effects 0.000 description 4
230000007306 turnover Effects 0.000 description 4
HOXGZVUCAYFWGR-KQQUZDAGSA-N (3e,5e)-octa-1,3,5-triene Chemical compound CC\C=C\C=C\C=C HOXGZVUCAYFWGR-KQQUZDAGSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000012696 Pd precursors Substances 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
MPAFPLNWSFVCCH-UHFFFAOYSA-N octa-2,7-dien-1-amine Chemical compound NCC=CCCCC=C MPAFPLNWSFVCCH-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
YHYGSIBXYYKYFB-VOTSOKGWSA-N (2e)-octa-2,7-dien-1-ol Chemical compound OC\C=C\CCCC=C YHYGSIBXYYKYFB-VOTSOKGWSA-N 0.000 description 2
ZTJHDEXGCKAXRZ-FNORWQNLSA-N (3e)-octa-1,3,7-triene Chemical compound C=CCC\C=C\C=C ZTJHDEXGCKAXRZ-FNORWQNLSA-N 0.000 description 2
SPFCXJSJGUQVKK-UHFFFAOYSA-M 1,3-bis(2,4,6-trimethylphenyl)imidazol-1-ium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC(C)=CC(C)=C1N1C=[N+](C=2C(=CC(C)=CC=2C)C)C=C1 SPFCXJSJGUQVKK-UHFFFAOYSA-M 0.000 description 2
OTOSIXGMLYKKOW-UHFFFAOYSA-M 1,3-bis(2,4,6-trimethylphenyl)imidazol-1-ium;chloride Chemical compound [Cl-].CC1=CC(C)=CC(C)=C1N1C=[N+](C=2C(=CC(C)=CC=2C)C)C=C1 OTOSIXGMLYKKOW-UHFFFAOYSA-M 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000001345 alkine derivatives Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
238000005336 cracking Methods 0.000 description 2
230000001955 cumulated effect Effects 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012847 fine chemical Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000003915 liquefied petroleum gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
150000002941 palladium compounds Chemical class 0.000 description 2
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 2
ZOUWOGOTHLRRLS-UHFFFAOYSA-N palladium;phosphane Chemical compound P.[Pd] ZOUWOGOTHLRRLS-UHFFFAOYSA-N 0.000 description 2
CUBIJGNGGJBNOC-UHFFFAOYSA-N palladium;tris(2-methylphenyl)phosphane Chemical compound [Pd].CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C.CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C CUBIJGNGGJBNOC-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
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Classifications

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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0214—Aryloxylates, e.g. phenolates
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/04—Formation or introduction of functional groups containing oxygen of ether, acetal or ketal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
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Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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Inorganic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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CA2449994A 2001-06-09 2002-05-04 Method for telomerizing non-cyclic olefins Expired - Fee Related CA2449994C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10128144.7		2001-06-09
DE10128144A DE10128144A1 (de)	2001-06-09	2001-06-09	Verfahren zur Telomerisation von nicht cyclischen Olefinen
PCT/EP2002/004909 WO2002100803A2 (de)	2001-06-09	2002-05-04	Verfahren zur telomerisation von nicht cyclischen olefinen

Publications (2)

Publication Number	Publication Date
CA2449994A1 CA2449994A1 (en)	2002-12-19
CA2449994C true CA2449994C (en)	2010-10-19

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Application Number	Title	Priority Date	Filing Date
CA2449994A Expired - Fee Related CA2449994C (en)	2001-06-09	2002-05-04	Method for telomerizing non-cyclic olefins

Country Status (20)

Country	Link
US (1)	US7026523B2 (cs)
EP (1)	EP1406852B1 (cs)
JP (1)	JP4090052B2 (cs)
KR (1)	KR100855517B1 (cs)
CN (1)	CN1297522C (cs)
AR (1)	AR034709A1 (cs)
AT (1)	ATE282017T1 (cs)
AU (1)	AU2002312879B2 (cs)
BR (1)	BR0210253A (cs)
CA (1)	CA2449994C (cs)
CZ (1)	CZ200433A3 (cs)
DE (2)	DE10128144A1 (cs)
EG (1)	EG23330A (cs)
ES (1)	ES2230498T3 (cs)
HU (1)	HUP0400235A3 (cs)
MX (1)	MXPA03011204A (cs)
NO (1)	NO329033B1 (cs)
PL (1)	PL207858B1 (cs)
TW (1)	TW591011B (cs)
WO (1)	WO2002100803A2 (cs)

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DE102007023515A1 (de)	2006-07-05	2008-01-10	Evonik Degussa Gmbh	Verfahren zur Herstellung von Dienen durch Hydrodimerisierung
US8393169B2 (en)	2007-09-19	2013-03-12	Emerson Climate Technologies, Inc.	Refrigeration monitoring system and method
US8558030B2 (en) *	2008-08-12	2013-10-15	Dow Global Technologies Llc	Process for telomerization of butadiene
DE102008046075A1 (de)	2008-09-08	2010-03-11	Evonik Röhm Gmbh	(Meth)acrylatmonomer, Polymer sowie Beschichtungsmittel
DE102009026819A1 (de)	2008-09-08	2010-03-11	Evonik Röhm Gmbh	Monomermischung, Polymer, Beschichtungsmittel und Verfahren zur Herstellung einer Beschichtung
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DE102010030970A1 (de)	2010-07-06	2012-01-12	Evonik Röhm Gmbh	Zusammensetzung zur Herstellung von Polymeren, (Meth)acryl-Polymer, Beschichtungsmittel und Beschichtung
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2001
- 2001-06-09 DE DE10128144A patent/DE10128144A1/de not_active Withdrawn
2002
- 2002-05-04 JP JP2003503574A patent/JP4090052B2/ja not_active Expired - Fee Related
- 2002-05-04 WO PCT/EP2002/004909 patent/WO2002100803A2/de not_active Ceased
- 2002-05-04 DE DE50201528T patent/DE50201528D1/de not_active Expired - Lifetime
- 2002-05-04 CN CNB028116127A patent/CN1297522C/zh not_active Expired - Fee Related
- 2002-05-04 HU HU0400235A patent/HUP0400235A3/hu unknown
- 2002-05-04 PL PL364370A patent/PL207858B1/pl unknown
- 2002-05-04 AT AT02738032T patent/ATE282017T1/de not_active IP Right Cessation
- 2002-05-04 US US10/478,697 patent/US7026523B2/en not_active Expired - Fee Related
- 2002-05-04 CA CA2449994A patent/CA2449994C/en not_active Expired - Fee Related
- 2002-05-04 KR KR1020037016073A patent/KR100855517B1/ko not_active Expired - Fee Related
- 2002-05-04 EP EP02738032A patent/EP1406852B1/de not_active Expired - Lifetime
- 2002-05-04 AU AU2002312879A patent/AU2002312879B2/en not_active Ceased
- 2002-05-04 BR BR0210253-6A patent/BR0210253A/pt not_active IP Right Cessation
- 2002-05-04 ES ES02738032T patent/ES2230498T3/es not_active Expired - Lifetime
- 2002-05-04 MX MXPA03011204A patent/MXPA03011204A/es active IP Right Grant
- 2002-05-04 CZ CZ200433A patent/CZ200433A3/cs unknown
- 2002-06-05 TW TW091112138A patent/TW591011B/zh not_active IP Right Cessation
- 2002-06-05 EG EG2002060608A patent/EG23330A/xx active
- 2002-06-07 AR ARP020102139A patent/AR034709A1/es active IP Right Grant
2003
- 2003-12-08 NO NO20035459A patent/NO329033B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUP0400235A2 (hu)	2004-12-28
CA2449994A1 (en)	2002-12-19
BR0210253A (pt)	2004-06-22
HUP0400235A3 (en)	2006-11-28
EP1406852A2 (de)	2004-04-14
WO2002100803A2 (de)	2002-12-19
CZ200433A3 (cs)	2004-12-15
DE50201528D1 (de)	2004-12-16
NO329033B1 (no)	2010-08-02
AR034709A1 (es)	2004-03-17
NO20035459D0 (no)	2003-12-08
KR20040043124A (ko)	2004-05-22
CN1297522C (zh)	2007-01-31
US20050038273A1 (en)	2005-02-17
ATE282017T1 (de)	2004-11-15
ES2230498T3 (es)	2005-05-01
PL207858B1 (pl)	2011-02-28
EG23330A (en)	2004-12-29
DE10128144A1 (de)	2002-12-12
EP1406852B1 (de)	2004-11-10
MXPA03011204A (es)	2004-02-26
US7026523B2 (en)	2006-04-11
KR100855517B1 (ko)	2008-09-02
CN1541197A (zh)	2004-10-27
JP4090052B2 (ja)	2008-05-28
PL364370A1 (en)	2004-12-13
TW591011B (en)	2004-06-11
JP2004534059A (ja)	2004-11-11
AU2002312879B2 (en)	2006-11-23
WO2002100803A3 (de)	2004-02-12

Legal Events

Date	Code	Title	Description
2006-12-19	EEER	Examination request
2016-06-15	MKLA	Lapsed	Effective date: 20160504

Publication	Publication Date	Title
US7026523B2 (en)	2006-04-11	Method for telomerizing non-cyclic olefins
CA2490332C (en)	2011-10-25	Process for the telomerization of acyclic olefins
KR100858837B1 (ko)	2008-09-17	팔라듐 카벤 화합물을 사용하는 1-올레핀의 제조방법
RU2279420C2 (ru)	2006-07-10	Способ получения 1-октена
KR101057588B1 (ko)	2011-08-19	금속 착물의 제조방법
HUP0401668A2 (hu)	2004-11-29	Javított hegeszthetőségű, optikai tulajdonságú és csökkentett oldhatóságú kristályos propilén kopolimer készítmények
US20050065387A1 (en)	2005-03-24	Method for the production of 1-octene by reductive telomerisation